CN111094310A - Organometallic compound and organic light emitting device including the same - Google Patents

Organometallic compound and organic light emitting device including the same Download PDF

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CN111094310A
CN111094310A CN201880057833.8A CN201880057833A CN111094310A CN 111094310 A CN111094310 A CN 111094310A CN 201880057833 A CN201880057833 A CN 201880057833A CN 111094310 A CN111094310 A CN 111094310A
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CN111094310B (en
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金曙渊
朴胎润
全相映
李东勋
李征夏
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LG Chem Ltd
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Abstract

The present invention provides an organometallic compound and an organic light emitting device including the same.

Description

Organometallic compound and organic light emitting device including the same
Technical Field
Cross Reference to Related Applications
This application claims priority or benefit to korean patent application No. 10-2017-0149679, filed on 10.11.2017 to the korean intellectual property office, the disclosure of which is incorporated herein by reference in its entirety.
The present invention relates to an organometallic compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon has characteristics such as a wide viewing angle, excellent contrast, a fast response time, excellent brightness, a driving voltage, and a response speed, and thus many studies have been made.
An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer generally has a multi-layer structure including different materials to improve efficiency and stability of the organic light emitting device, and for example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic material layer, electrons are injected from a cathode into the organic material layer, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall to a ground state again.
There is a continuing need to develop new materials for organic materials used in organic light emitting devices as described above.
[ Prior art documents ]
[ patent document ]
(patent document 0001) Korean unexamined patent publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
An object of the present invention is to provide a novel organometallic compound and an organic light emitting device including the same.
Technical scheme
In one aspect of the present invention, there is provided a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure BDA0002401864950000021
Wherein, in chemical formula 1,
x is O, S, NH or Se, and the formula is shown in the specification,
R1is-Si (R)a)(Rb)(Rc)，
Wherein R isa、RbAnd RcIs hydrogen, deuterium, or substituted or unsubstituted C1-10An alkyl group, a carboxyl group,
R2、R3and R4Each independently is hydrogen; deuterium; halogen; a cyano group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60A haloalkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C1-60A haloalkoxy group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C6-60An aryloxy group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S2-60A heterocyclic group,
a and b are each 0 and 1, or 1 and 0, respectively, and
n is 1 or 2.
In another aspect of the present invention, there is provided an organic light emitting device including a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers is a light emitting layer, and wherein the light emitting layer includes the compound represented by chemical formula 1.
Advantageous effects
The compound represented by chemical formula 1 described above may be used as a material of an organic material layer of an organic light emitting device, and may improve efficiency, achieve a low driving voltage, and/or improve lifetime characteristics in the organic light emitting device. In particular, the compound represented by chemical formula 1 may be used as a material of the light emitting layer.
Drawings
Fig. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4.
Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4.
Detailed Description
Hereinafter, embodiments of the present invention will be described in more detail to help understanding of the present invention.
As used herein, a symbol
Figure BDA0002401864950000031
Meaning a bond to another substituent.
As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; and a heterocyclic group comprising at least one of N, O and the S atom, or a substituent that is unsubstituted or linked by two or more of the substituents exemplified above. For example, "a substituent to which two or more substituents are attached" may be a biphenyl group. That is, biphenyl can be aryl, and can also be interpreted as a substituent with two phenyl groups attached.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a compound having the following structural formula, but is not limited thereto.
Figure BDA0002401864950000041
In the present specification, the ester group may have a structure in which the oxygen of the ester group may be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto.
Figure BDA0002401864950000042
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a compound having the following structural formula, but is not limited thereto.
Figure BDA0002401864950000043
In the present specification, the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is from 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 10. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-butyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is from 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is from 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is from 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl, styryl and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the number of carbon atoms of the cycloalkyl group is from 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is from 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is from 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 20. As the monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. The polycyclic aryl groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,
Figure BDA0002401864950000051
A phenyl group, a fluorenyl group, and the like, but are not limited thereto.
In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure. In the case of substituted fluorenyl radicals, may form
Figure BDA0002401864950000061
And the like. However, the structure is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Figure BDA0002401864950000062
Azolyl group,
Figure BDA0002401864950000063
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Figure BDA0002401864950000064
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, isoquinoyl
Figure BDA0002401864950000065
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group of the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the foregoing examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group and the alkylamino group is the same as the foregoing examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine may employ the aforementioned description of the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the foregoing example of the alkenyl group. In this specification, the foregoing description of aryl groups may be applied with the exception that the arylene group is a divalent group. In this specification, the foregoing description of heterocyclyl groups may be applied with the difference that the heteroarylene group is a divalent group. In this specification, the foregoing description of aryl or cycloalkyl groups may be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present specification, the foregoing description of a heterocyclic group may be applied except that the heterocyclic group is not a monovalent group but is formed by combining two substituents.
According to R in chemical formula 11The substitution position of chemical formula 1 may be represented by the following chemical formula 1-1, 1-2, 1-3, 1-4 or 1-5.
Figure BDA0002401864950000071
Preferably, R1is-Si (CH)3)3。
Preferably, R2Is hydrogen, methyl, CD3Ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
Preferably, R3Is hydrogen or methyl、CD3Ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
Preferably, R4Is hydrogen.
Further, preferably, the triplet energy level of the compound represented by chemical formula 1 is 2.6eV or less, more preferably 2.45eV to 2.6 eV.
Further, it is preferable that the maximum light emission wavelength of the compound represented by chemical formula 1 is 500nm to 550nm, more preferably 520nm to 535 nm.
Representative examples of the compound represented by chemical formula 1 are as follows.
Figure BDA0002401864950000081
Figure BDA0002401864950000091
Figure BDA0002401864950000101
Figure BDA0002401864950000111
Figure BDA0002401864950000121
Figure BDA0002401864950000131
Figure BDA0002401864950000141
Figure BDA0002401864950000151
Figure BDA0002401864950000161
Figure BDA0002401864950000171
Figure BDA0002401864950000181
Figure BDA0002401864950000191
Figure BDA0002401864950000201
Figure BDA0002401864950000211
Figure BDA0002401864950000221
Figure BDA0002401864950000231
Figure BDA0002401864950000241
Figure BDA0002401864950000251
Figure BDA0002401864950000261
Figure BDA0002401864950000271
Figure BDA0002401864950000281
Figure BDA0002401864950000291
Figure BDA0002401864950000301
Figure BDA0002401864950000311
Figure BDA0002401864950000321
Figure BDA0002401864950000331
Figure BDA0002401864950000341
Figure BDA0002401864950000351
Figure BDA0002401864950000361
Figure BDA0002401864950000371
Figure BDA0002401864950000381
Figure BDA0002401864950000391
Figure BDA0002401864950000401
Figure BDA0002401864950000411
Figure BDA0002401864950000421
Figure BDA0002401864950000431
Figure BDA0002401864950000441
Figure BDA0002401864950000451
Figure BDA0002401864950000461
Figure BDA0002401864950000471
Figure BDA0002401864950000481
Figure BDA0002401864950000491
Figure BDA0002401864950000501
Figure BDA0002401864950000511
The compound represented by chemical formula 1 may be prepared by a preparation method as shown in reaction scheme 1.
[ reaction scheme 1]
Figure BDA0002401864950000521
The above production method will be more specifically described in the production examples described below.
In another embodiment of the present invention, there is provided an organic light emitting device comprising the compound represented by chemical formula 1 described above. As an example, an organic light emitting device is provided, which includes a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers is a light emitting layer, and wherein the light emitting layer includes the compound represented by chemical formula 1.
The organic material layer of the organic light emitting device of the present invention may have a single layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it may include a smaller number of organic layers.
In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, fig. 1 and 2 show the structure of an organic light emitting device according to an embodiment of the present invention.
Fig. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be included in the light emitting layer.
Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be included in the light emitting layer.
The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that one or more layers of the organic material layer include the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by the following process: a metal, a metal oxide having conductivity, or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a material that can be used as a cathode is deposited on the organic material layer. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, in manufacturing the organic light emitting device, the compound represented by chemical formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (international publication WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
As the anode material, in general, it is preferable to use a material having a large work function so that holes can be smoothly injected into the organic material layer.Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SnO2Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.
As the cathode material, in general, it is preferable to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al; and the like, but are not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound of: it has an ability to transport holes, and thus has a hole injection effect in the anode and an excellent hole injection effect to the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material, and is excellent in an ability to form a thin film. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanenitrile-based hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone-based, polyaniline-based, and polythiophene-based conductive polymers, and the like, but are not limited thereto.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having a large hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers in which a conjugated portion and a non-conjugated portion coexist, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of the heterocycle-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
The dopant material may be an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, or the like. In particular, in the present invention, the compound represented by chemical formula 1 is used as a dopant.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is suitably a material that can well receive electrons from the cathode and transport the electrons to the light emitting layer and has a large electron mobility. Specific examples thereof include: al complexes of 8-hydroxyquinoline; comprising Alq3The complex of (1); an organic radical compound; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used according to the related art. Suitable examples of cathode materials are, in particular, typical materials having a low work function, followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.
The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound of: it has an ability to transport electrons, has an effect of injecting electrons from a cathode and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons generated from the light emitting layer from moving to a hole injection layer, and is also excellent in an ability to form a thin film. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and mixtures thereof,
Figure BDA0002401864950000551
Azole,
Figure BDA0002401864950000552
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex compounds include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), chlorogallium bis (2-methyl-8-quinolinolato), gallium bis (2-methyl-8-quinolino) (o-cresol), aluminum bis (2-methyl-8-quinolino) (1-naphthol), gallium bis (2-methyl-8-quinolino) (2-naphthol), and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a front side emission type, a rear side emission type, or a double side emission type depending on the material used.
In addition, the compound represented by chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
The preparation of the compound represented by chemical formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of the present invention.
[ preparation examples ]
Preparation examples 1 to 1: preparation of Compounds A1 and B1
Figure BDA0002401864950000553
(1) Preparation of Compound A1
After 2-bromopyridine (50g, 0.32mol) and phenylboronic acid (43g, 0.35mol) were dissolved in tetrahydrofuran in a round-bottom flask under a nitrogen atmosphere, 2M aqueous potassium carbonate (250ml) was added and tetrakis (triphenylphosphine) palladium (7.4g, 6.4mmol) was added, and then the mixture was heated and stirred at 80 ℃ for 12 hours. After the reaction was completed, the temperature was lowered, the aqueous layer was separated, and the organic layer solvent was removed. The reaction mixture was dissolved in chloroform and then washed with water. To this was added magnesium sulfate and acidic clay, stirred, filtered and concentrated under reduced pressure. Subsequently, the resulting product was subjected to column chromatography under the conditions of ethyl acetate: hexane ═ 1:50 (v: v) to give compound a1(41g, yield: 82%).
(2) Preparation of Compound 1-1a
Iridium chloride (10g, 33mmol) and Compound A1(11.4g, 0.073mol) were added to 2-ethoxyethanol (1000ml) and distilled water (330ml) in a round-bottomed flask, and the mixture was heated and stirred for 24 hours. The reaction mixture was cooled to room temperature, filtered, and washed with 2L of ethanol to give compound 1-1b (9.7g, yield: 55%) as a solid.
(3) Preparation of Compound B1
After dissolving compound 1-1b (9.7g, 9mmol) in dichloromethane (500ml), AgOTf (14.6g, 18.9mmol) was dissolved in methanol (250ml) and added thereto, and the mixture was stirred at room temperature while blocking light. After 24 hours, the resulting mixture was filtered to remove the solvent of the filtrate and precipitated with toluene to give compound B1 without further purification (yield: 93%).
Preparation examples 1 to 2: preparation of Compounds A2 and B2
Figure BDA0002401864950000561
(1) Preparation of Compound A2
Compound A2(28g, yield: 80%) was prepared in the same manner as in the process for preparing Compound A1, except that 2-bromo-5-methylpyridine (35.0g, 0.20mol) was used instead of 2-bromopyridine.
(2) Preparation of Compound 1-1b
Compound 1-1b (10g, yield: 57%) was prepared in the same manner as in the method for preparing compound 1-1a, except that compound a2 was used instead of compound a 1.
(3) Preparation of Compound B2
Compound B2 (yield: 92%) was prepared in the same manner as in the method for preparing compound B1, except that compound 1-1B was used instead of compound 1-1 a.
Preparation examples 1 to 3: preparation of Compounds A3 and B3
Figure BDA0002401864950000571
(1) Preparation of Compounds 1-1c
After 2, 5-bromopyridine (55g, 0.23mol) and phenylboronic acid (31g, 0.25mol) were dissolved in acetonitrile (200ml) and methanol (200ml) in a round-bottomed flask under a nitrogen atmosphere, 2M aqueous potassium carbonate (150ml) was added and tetrakis (triphenylphosphine) palladium (7.4g, 6.4mmol) was added, and then the mixture was heated and stirred at 50 ℃ for 18 hours. After the reaction was completed, the temperature was lowered, the aqueous layer was separated, and then the organic layer solvent was removed. The reaction mixture was dissolved in chloroform and then washed with water. To this was added magnesium sulfate and acidic clay, stirred, filtered and concentrated under reduced pressure. Subsequently, the obtained product was subjected to column chromatography under the conditions of hexane: dichloromethane ═ 1:100 (v: v) to obtain compound 1-1c (41g, yield: 76%).
(2) Preparation of Compounds 1-1d
After 5-bromo-2-phenylpyridine (41g, 0.17mol) was dissolved in diethyl ether in a round-bottom flask under a nitrogen atmosphere, 2.5M n-BuLi (12g, 0.18mol) was added thereto at-78 ℃ and then stirred for one hour. Triethyl borate (37g, 0.25mol) was added thereto at-78 deg.C, followed by stirring at room temperature for 4 hours. 2M aqueous hydrochloric acid (100ml) was added and stirred for 30 minutes, followed by neutralization with 20% aqueous sodium hydroxide (100 ml). The aqueous layer was separated and then the organic layer solvent was removed. The resulting product was subjected to column chromatography under the conditions of hexane: dichloromethane ═ 1:100 (v: v) to obtain compound 1-1d (15g, yield: 45%).
(3) Preparation of Compound A3
After (6-phenylpyridin-3-yl) boronic acid (15g, 0.076mol) and iodomethane-d 3(24.6g, 0.17mol) were dissolved in tetrahydrofuran (150ml) and methanol (70ml) in a round bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (100ml) was added and tetrakis (triphenylphosphine) palladium (2.6g, 2.3mmol) was added, and the mixture was heated and stirred at 40 ℃ for 16 hours. The reaction mixture was dissolved in chloroform and then washed with water. To this was added magnesium sulfate and acidic clay, stirred, filtered and concentrated under reduced pressure. Subsequently, the obtained product was subjected to column chromatography under the conditions of hexane: ethyl acetate ═ 1:50 (v: v) to obtain compound a3(6.9g, yield: 53%).
(4) Preparation of Compounds 1-1e
Compound 1-1e (4g, yield: 60%) was prepared in the same manner as in the method for preparing Compound 1-1a, except that Compound A3 was used instead of Compound A1.
(5) Preparation of Compound B3
Compound B3 (yield: 96%) was prepared in the same manner as in the method for preparing compound B1, except that compound 1-1e was used instead of compound 1-1 a.
Preparation examples 1 to 4: preparation of Compounds A4 and B4
Figure BDA0002401864950000581
(1) Preparation of Compound A4
Compound a4(14g, yield: 78%) was prepared in the same manner as in the method for preparing compound A3, except that iodocyclopropane was used instead of iodomethane-d 3.
(2) Preparation of Compounds 1-1f
Compound 1-1f (8g, yield: 63%) was prepared in the same manner as in the method for preparing compound 1-1a, except that compound a4 was used instead of compound a 1.
(3) Preparation of Compound B4
Compound B4 (yield: 91%) was prepared in the same manner as in the method for preparing compound B1, except that compound 1-1f was used instead of compound 1-1 a.
Preparation examples 1 to 5: preparation of Compounds A5 and B5
Figure BDA0002401864950000591
(1) Preparation of Compound A5
Compound a5(23g, yield: 69%) was prepared in the same manner as in the method for preparing compound A3, except that iodocyclopentane was used instead of iodomethane-d 3.
(2) Preparation of Compound 1-1g
Compound 1-1g (12g, yield: 52%) was prepared in the same manner as in the method for preparing Compound 1-1a, except that Compound A5 was used instead of Compound A1.
(3) Preparation of Compound B5
Compound B5 (yield: 93%) was prepared in the same manner as in the method for preparing compound B1, except that compound 1-1g was used instead of compound 1-1 a.
Preparation examples 1 to 6: preparation of Compounds A6 and B6
Figure BDA0002401864950000592
(1) Preparation of Compound A6
Compound a6(18g, yield: 64%) was prepared in the same manner as in the method for preparing compound A3, except that iodocyclohexane was used instead of iodomethane-d 3.
(2) Preparation of Compounds 1-1h
Compound 1-1g (9.4g, yield: 53%) was prepared in the same manner as in the method for preparing Compound 1-1a, except that Compound A6 was used instead of Compound A1.
(3) Preparation of Compound B5
Compound B6 (yield: 95%) was prepared in the same manner as in the method for preparing compound B1, except that compound 1-1h was used instead of compound 1-1 a.
Preparation example 2-1: preparation of Compounds C1 and D1
Figure BDA0002401864950000601
(1) Preparation of Compound C1
After 2-bromopyridine (50g, 0.32mol) and 4- (dibenzofuranyl) boronic acid (71g, 0.34mol) were dissolved in tetrahydrofuran (500ml) and methanol (250ml) in a round-bottomed flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (250ml) was added and tetrakis (triphenylphosphine) palladium (7.4g, 6.4mmol) was added, and then the mixture was heated and stirred at 80 ℃ for 8 hours. After the reaction was completed, the temperature was lowered, the aqueous layer was separated, and then the organic layer solvent was removed. The reaction mixture was dissolved in chloroform and then washed with water. To this was added magnesium sulfate and acidic clay, stirred, filtered and concentrated under reduced pressure. Subsequently, the resulting product was subjected to column chromatography under the conditions of ethyl acetate: hexane ═ 1:50 (v: v) to give compound C1(69g, yield: 88%).
(2) Preparation of Compound 2-1a
Compound 2-1a (21g, yield: 48%) was prepared in the same manner as in the method for preparing compound 1-1a, except that compound C1 was used instead of compound a 1.
(3) Preparation of Compound D1
Compound D1 (yield: 93%) was prepared in the same manner as in the method for preparing compound B1, except that compound 2-1a was used instead of compound 1-1 a.
Preparation examples 2 to 2: preparation of Compounds C2 and D2
Figure BDA0002401864950000611
(1) Preparation of Compound 2-1b
Compound 2-1b (52g, yield: 81%) was prepared in the same manner as in the method for preparing compound C1, except that (6-bromodibenzo [ b, d ] furan-4-yl) boronic acid was used instead of (4-dibenzofuranyl) boronic acid.
(2) Preparation of Compound C2
After compound 2-1b (20g, 0.061mol) was dissolved in tetrahydrofuran (400ml) in a round-bottomed flask under a nitrogen atmosphere, 2.5M n-BuLi (4.3g, 0.67mol) was added thereto at-78 ℃ and then stirred for 1 hour. Chlorotrimethylsilane (10.0g, 0.10mol) was added thereto at-78 ℃ and the mixture was stirred at room temperature for 10 hours. The organic layer was extracted with dichloromethane, to which magnesium sulfate and acidic clay were added, stirred, filtered and concentrated under reduced pressure. Subsequently, the obtained product was subjected to column chromatography under the conditions of hexane: ethyl acetate ═ 1:50 (v: v) to obtain compound C2(13g, yield: 65%).
(3) Preparation of Compound 2-1c
Compound 2-1C (6g, yield: 54%) was prepared in the same manner as in the method for preparing compound 1-1a, except that compound C2 was used instead of compound a 1.
(4) Preparation of Compound D2
Compound D2 (yield: 90%) was prepared in the same manner as in the method for preparing compound B1, except that compound 2-1c was used instead of compound 1-1 a.
Preparation examples 2 to 3: preparation of Compounds C3 and D3
Figure BDA0002401864950000621
(1) Preparation of Compounds 2-1d
Compound 2-1d (60g, yield: 84%) was prepared in the same manner as in the method for preparing compound C1, except that (7-bromodibenzo [ b, d ] furan-4-yl) boronic acid was used instead of 4- (dibenzofuranyl) boronic acid.
(2) Preparation of Compound C3
Compound C3(53g, yield: 91%) was prepared in the same manner as in the method for preparing compound C2, except that compound 2-1d was used instead of compound 2-1 b.
(3) Preparation of Compound 2-1e
Compound 2-1e (26g, yield: 55%) was prepared in the same manner as in the method for preparing compound 1-1a, except that compound C3 was used instead of compound a 1.
(4) Preparation of Compound D3
Compound D3 (yield: 93%) was prepared in the same manner as in the method for preparing compound B1, except that compound 2-1e was used instead of compound 1-1 a.
Preparation examples 2 to 4: preparation of Compounds C4 and D4
Figure BDA0002401864950000622
(1) Preparation of Compounds 2-1d
Compound 2-1f (54g, yield: 77%) was prepared in the same manner as in the method for preparing compound C1, except that (8-bromodibenzo [ b, d ] furan-4-yl) boronic acid was used instead of 4- (dibenzofuranyl) boronic acid.
(2) Preparation of Compound C4
Compound C4(49g, yield: 92%) was prepared in the same manner as in the method for preparing compound C2, except that compound 2-1f was used instead of compound 2-1 b.
(3) Preparation of Compound 2-1g
Compound 2-1g (28g, yield: 54%) was prepared in the same manner as in the method for preparing Compound 1-1a, except that Compound C4 was used instead of Compound A1.
(4) Preparation of Compound D4
Compound D4 (yield: 92%) was prepared in the same manner as in the method for preparing compound B1, except that compound 2-1g was used instead of compound 1-1 a.
Preparation examples 2 to 5: preparation of Compounds C5 and D5
Figure BDA0002401864950000631
(1) Preparation of Compound 2-1h
Compound 2-1h (66g, yield: 82%) was prepared in the same manner as in the method for preparing compound C1, except that (9-bromodibenzo [ b, d ] furan-4-yl) boronic acid was used instead of 4- (dibenzofuranyl) boronic acid.
(2) Preparation of Compound C5
Compound C5(47g, yield: 78%) was prepared in the same manner as in the method for preparing compound C2, except that compound 2-1h was used instead of compound 2-1 b.
(3) Preparation of Compound 2-1i
Compound 2-1i (22g, yield: 48%) was prepared in the same manner as in the method for preparing compound 1-1a, except that compound C5 was used instead of compound a 1.
(4) Preparation of Compound D5
Compound D5 (yield: 90%) was prepared in the same manner as in the method for preparing compound B1, except that compound 2-1i was used instead of compound 1-1 a.
[ examples ]
Example 1: preparation of Compound 1
Figure BDA0002401864950000641
Compound B1(10.2g, 14mmol), compound C2(11g, 35mmol), methanol (100ml) and ethanol (100ml) were added under a nitrogen atmosphere, the mixture was heated and stirred at 80 ℃ for 48 hours. After completion of the reaction, the reaction mixture was filtered and washed with ethanol, and subjected to column chromatography under the conditions of hexane: ethyl acetate ═ 1:5 (volume: volume) to obtain compound 1 (yield: 37%).
MS：[M+H]+＝818.3
Example 2: preparation of Compound 2
Figure BDA0002401864950000642
Compound 2 was prepared in the same manner as in the method for preparing compound 1 (yield: 49%) except that compound C3 was used instead of compound C2.
MS：[M+H]+＝818.3
Example 3: preparation of Compound 3
Figure BDA0002401864950000643
Compound 3 was prepared in the same manner as in the method for preparing compound 1 (yield: 41%) except that compound C4 was used instead of compound C2.
MS：[M+H]+＝818.3
Example 4: preparation of Compound 4
Figure BDA0002401864950000651
Compound 4 was prepared in the same manner as in the method for preparing compound 1 (yield: 38%) except that compound C5 was used instead of compound C2.
MS：[M+H]+＝818.3
Example 5: preparation of Compound 5
Figure BDA0002401864950000652
Compound 5 (yield: 51%) was prepared in the same manner as in the method for preparing compound 1, except that compound B2 was used instead of compound B1.
MS：[M+H]+＝846.3
Example 6: preparation of Compound 6
Figure BDA0002401864950000653
Compound 6 was prepared in the same manner as in the method for preparing compound 1 (yield: 49%) except that compound B2 and compound C2 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝846.3
Example 7: preparation of Compound 7
Figure BDA0002401864950000661
Compound 7 was prepared in the same manner as in the method for preparing compound 1 (yield: 43%) except that compound B2 and compound C4 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝846.3
Example 8: preparation of Compound 8
Figure BDA0002401864950000662
Compound 8 was prepared in the same manner as in the method for preparing compound 1 (yield: 51%) except that compound B2 and compound C5 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝846.3
Example 9: preparation of Compound 9
Figure BDA0002401864950000663
Compound 9 (yield: 45%) was prepared in the same manner as in the method for preparing compound 1, except that compound B3 was used instead of compound B1.
MS：[M+H]+＝852.3
Example 10: preparation of Compound 10
Figure BDA0002401864950000671
Compound 10 was prepared in the same manner as in the method for preparing compound 1 (yield 39%) except that compound B3 and compound C3 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝852.3
Example 11: preparation of Compound 11
Figure BDA0002401864950000672
Compound 11 was prepared in the same manner as in the method for preparing compound 1 (yield 45%) except that compound B3 and compound C4 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝852.3
Example 12: preparation of Compound 12
Figure BDA0002401864950000673
Compound 12 was prepared in the same manner as in the method for preparing compound 1 (yield 45%) except that compound B3 and compound C5 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝852.3
Example 13: preparation of Compound 13
Figure BDA0002401864950000681
Compound 13 was prepared in the same manner as in the method for preparing compound 1 (yield 41%) except that compound B4 was used instead of compound B1.
MS：[M+H]+＝898.3
Example 14: preparation of Compound 14
Figure BDA0002401864950000682
Compound 14 was prepared in the same manner as in the method for preparing compound 1 (yield 41%) except that compound B4 and compound C3 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝898.3
Example 15: preparation of Compound 15
Figure BDA0002401864950000683
Compound 15 (yield: 38%) was prepared in the same manner as in the method for preparing compound 1, except that compound B4 and compound C4 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝898.3
Example 16: preparation of Compound 16
Figure BDA0002401864950000691
Compound 16 (yield: 45%) was prepared in the same manner as in the method for preparing compound 1, except that compound B4 and compound C5 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝898.3
Example 17: preparation of Compound 17
Figure BDA0002401864950000692
Compound 17 (yield: 43%) was prepared in the same manner as in the method for preparing compound 1, except that compound B5 was used instead of compound B1.
MS：[M+H]+＝954.4
Example 18: preparation of Compound 18
Figure BDA0002401864950000693
Compound 18 was prepared in the same manner as in the method for preparing compound 1 (yield: 40%) except that compound B5 and compound C3 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝954.4
Example 19: preparation of Compound 19
Figure BDA0002401864950000701
Compound 19 (yield: 41%) was prepared in the same manner as in the method for preparing compound 1, except that compound B5 and compound C4 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝954.4
Example 20: preparation of Compound 20
Figure BDA0002401864950000702
Compound 20 was prepared in the same manner as in the method for preparing compound 1 (yield: 44%) except that compound B5 and compound C5 were used instead of compound B1 and compound C2.
MS：[M+H]+＝954.4
Example 21: preparation of Compound 21
Figure BDA0002401864950000703
Compound 21 (yield: 39%) was prepared in the same manner as in the method for preparing compound 1, except that compound B6 was used instead of compound B1.
MS：[M+H]+＝982.4
Example 22: preparation of Compound 22
Figure BDA0002401864950000711
Compound 22 was prepared in the same manner as in the method for preparing compound 1 (yield: 48%) except that compound B6 and compound C3 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝982.4
Example 23: preparation of Compound 23
Figure BDA0002401864950000712
Compound 23 was prepared in the same manner as in the method for preparing compound 1 (yield: 46%) except that compound B6 and compound C4 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝982.4
Example 24: preparation of Compound 24
Figure BDA0002401864950000713
Compound 24 was prepared in the same manner as in the method for preparing compound 1 (yield: 46%) except that compound B6 and compound C5 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝982.4
Example 25: preparation of Compound 25
Figure BDA0002401864950000721
Compound 25 was prepared in the same manner as in the method for preparing compound 1 (yield: 39%) except that compound D2 and compound a1 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝980.3
Example 26: preparation of Compound 26
Figure BDA0002401864950000722
Compound 26 was prepared in the same manner as in the method for preparing compound 1 (yield: 42%) except that compound D3 and compound a1 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝980.3
Example 27: preparation of Compound 27
Figure BDA0002401864950000723
Compound 27 was prepared in the same manner as in the method for preparing compound 1 (yield: 39%) except that compound D4 and compound a1 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝980.3
Example 28: preparation of Compound 28
Figure BDA0002401864950000731
Compound 28 was prepared in the same manner as in the method for preparing compound 1 (yield: 35%) except that compound D5 and compound a1 were used instead of compound B1 and compound C2, respectively.
MS：[M+H]+＝980.3
[ Experimental example ]
Experimental example 1
Is coated thereon with a thickness of
Figure BDA0002401864950000732
The ITO (indium tin oxide) as a glass substrate of the thin film was put in distilled water in which a detergent was dissolved, and ultrasonically cleaned. At this time, a product manufactured by Fischer co. was used as a cleaning agent, and as distilled water, distilled water filtered twice with a filter manufactured by Millipore co. was used. After the ITO was cleaned for 30 minutes, the ultrasonic cleaning was repeated twice for 10 minutes using distilled water. After the completion of the cleaning with distilled water, the substrate was ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes and then transferred to a vacuum depositor.
On the ITO transparent electrode thus prepared, the following compound HI-1 was added
Figure BDA0002401864950000733
Is thermally vacuum deposited to form a hole injection layer. On the hole injection layer, the following compound HT-1 and
Figure BDA0002401864950000734
is thermally vacuum deposited to form a hole transport layer, and the following compound HT-2 is deposited on the HT-1 layer
Figure BDA0002401864950000735
Is vacuum deposited to form an electron blocking layer. Then, the following compound H1, the following compound H2, and the previously prepared compound 1 were co-deposited on the HT-2 deposition layer at a weight ratio of 44:44:12 as a host to form a layer having a thickness of
Figure BDA0002401864950000736
The light emitting layer of (1). The following compound ET-1 is added on the light-emitting layer
Figure BDA0002401864950000737
Is deposited under vacuum and the following compound ET-2 is further co-deposited with 2% by weight of Li to
Figure BDA0002401864950000738
To form an electron transport layer and an electron injection layer. Aluminum is deposited on the electron injection layer
Figure BDA0002401864950000739
Is deposited to form the cathode.
Figure BDA0002401864950000741
In the above process, the vapor deposition rate of the organic material is maintained at
Figure BDA0002401864950000742
Second to
Figure BDA0002401864950000743
Second, the deposition rate of aluminum is maintained at
Figure BDA0002401864950000744
Second, the degree of vacuum during deposition was maintained at 1X 10-7Hold in the palm to 5 x 10-8And (4) supporting.
Experimental examples 2 to 7
An organic light-emitting device was fabricated in the same manner as in experimental example 1, except that the compounds shown in table 2 below were used in place of compound 1 in forming the light-emitting layer.
Comparative Experimental examples 1 to 4
An organic light emitting device was fabricated in the same manner as in experimental example 1, except that the compounds shown in table 2 below were used as dopants in forming a light emitting layer instead of compound 1. In Table 1 below, the compound Ir (ppy)3E1, E2 and E3 are as follows.
Figure BDA0002401864950000751
Compounds 1, 9, 25 and Ir (ppy) used in the examples and comparative examples3E1 to E3 measurement of HOMO, LUMO and T1(triplet energy level) the results are shown in table 1 below.
[ Table 1]
Dopant material HOMO(eV) LUMO(eV) T1(eV)
Compound 1 5.34 2.56 2.56
Compound 9 5.29 2.52 2.57
Compound 25 5.27 2.56 2.45
Ir(ppy)3 5.12 2.10 2.59
E1 5.44 2.15 2.63
E2 5.58 2.30 2.72
E3 5.25 2.47 2.58
In addition, the maximum light emission wavelength (λ max), voltage, efficiency, color coordinates, and lifetime were measured by applying current to the organic light emitting devices manufactured in the experimental example and the comparative experimental example, and the results are shown in table 2 below. T95 means the time required for the luminance to decrease to 95% of the initial luminance.
[ Table 2]
Figure BDA0002401864950000752
As shown in Table 2, the compounds Ir (ppy)3When the compound of the present invention is used as a phosphorescent dopant material, it exhibits excellent characteristics in terms of lifetime, as compared to comparative examples. This confirms that silyl substituents affect lifetime. In addition, in the case of experimental examples 1, 5, 7 and 9, the life characteristic was increased up to 200% as compared with comparative example 2. From the above results, it can be seen that the difference in lifetime is significant depending on the presence or absence of the silyl substituent and the position of the substitution.
[ description of reference numerals ]
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light-emitting layer 8: electron transport layer

Claims (9)

1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure FDA0002401864940000011
Wherein, in chemical formula 1,
x is O, S, NH or Se, and the formula is shown in the specification,
R1is-Si (R)a)(Rb)(Rc)，
Wherein R isa、RbAnd RcIs hydrogen, deuterium, or substituted or unsubstituted C1-10An alkyl group, a carboxyl group,
R2、R3and R4Each independently is hydrogen; deuterium; halogen; a cyano group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60A haloalkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C1-60A haloalkoxy group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C6-60An aryloxy group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S2-60A heterocyclic group,
a and b are each 0 and 1, or 1 and 0, respectively, and
n is 1 or 2.
2. The compound of claim 1, wherein
R1is-Si (CH)3)3。
3. The compound of claim 1, wherein
R2Is hydrogen, methyl, CD3Ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
4. The compound of claim 1, wherein
R3Is hydrogen, methyl, CD3Ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
5. The compound of claim 1, wherein
R4Is hydrogen.
6. The compound of claim 1, wherein
The triplet energy level of the compound is 2.6eV or less.
7. The compound of claim 1, wherein
The maximum light-emitting wavelength of the compound is 500nm to 550 nm.
8. The compound of claim 1, wherein
The compound represented by chemical formula 1 is any one selected from the group consisting of:
Figure FDA0002401864940000031
Figure FDA0002401864940000041
Figure FDA0002401864940000051
Figure FDA0002401864940000061
Figure FDA0002401864940000071
Figure FDA0002401864940000081
Figure FDA0002401864940000091
Figure FDA0002401864940000101
Figure FDA0002401864940000111
Figure FDA0002401864940000121
Figure FDA0002401864940000131
Figure FDA0002401864940000141
Figure FDA0002401864940000151
Figure FDA0002401864940000161
Figure FDA0002401864940000171
Figure FDA0002401864940000181
Figure FDA0002401864940000191
Figure FDA0002401864940000201
Figure FDA0002401864940000211
Figure FDA0002401864940000221
Figure FDA0002401864940000231
Figure FDA0002401864940000241
Figure FDA0002401864940000251
Figure FDA0002401864940000261
Figure FDA0002401864940000271
Figure FDA0002401864940000281
Figure FDA0002401864940000291
Figure FDA0002401864940000301
Figure FDA0002401864940000311
Figure FDA0002401864940000321
Figure FDA0002401864940000331
Figure FDA0002401864940000341
Figure FDA0002401864940000351
Figure FDA0002401864940000361
Figure FDA0002401864940000371
Figure FDA0002401864940000381
Figure FDA0002401864940000391
Figure FDA0002401864940000401
Figure FDA0002401864940000411
Figure FDA0002401864940000421
Figure FDA0002401864940000431
Figure FDA0002401864940000441
Figure FDA0002401864940000451
Figure FDA0002401864940000461
9. an organic light emitting device includes a first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers is a light-emitting layer, and wherein the light-emitting layer comprises the compound according to any one of claims 1 to 8.
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